t-Butylaminodimethylsilylchloride → HCID 18544243, compound

HRID 1268147Notes

Reaction equation

HRID 1268147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([Li])[CH:7]=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:21][C:22]([NH:25][Si:26](Cl)([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([Si:26]([CH3:28])([CH3:27])[NH:25][C:22]([CH3:24])([CH3:23])[CH3:21])[CH:7]=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11205972t-ButylaminodimethylsilylchlorideHCID 178506816HCID 178506816, compound

Product 1

HCID 18544243HCID 18544243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(5,6-dimethoxy-3-phenyl-1H-inden-1-yl)lithium (1.24 g, 4.8 mmol) was dissolved in 20 mL of THF and added to a solution of N-(tert-butyl)-N-(1-chloro-1,1-dimethylsilyl)amine (1.035 g, 6.24 mmol) in 50 mL of THF over a 25 min period, with stirring continued for 20 h. The solution was then evaporated under reduced pressure and the residue was extracted with hexane (50 mL). After filtration, the solvent was removed under reduced pressure. To this residue, 30 mL of hexane was added and the flask was put aside into a freezer (−27° C.) for 2 days. After that time the crystallized solid was filtered off and the solvent was removed leaving 1.68 of the product as a yellow oil.

Workup

  1. customThe solution was then evaporated under reduced pressure
  2. extractionthe residue was extracted with hexane (50 mL)
  3. filtrationAfter filtration
  4. customthe solvent was removed under reduced pressure
  5. additionTo this residue, 30 mL of hexane was added
  6. waitthe flask was put aside into a freezer (−27° C.) for 2 days
  7. filtrationAfter that time the crystallized solid was filtered off
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-e27e97b0ddd24c97bf64cffba4653e59
Source dataset
uspto-grants-2003_04
Patent number
US06555634B1

Reaction notes

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